在自由基催化下，烯烴或炔烴和烯基環(huán)丙烷反應(yīng)得到烯基環(huán)戊烷或烯基環(huán)戊烯的反應(yīng)。類似反應(yīng)：Vinylcyclopropane-cyclopentene rearrangement（烯基環(huán)丙烷-環(huán)戊烯重排）
反應(yīng)機(jī)理
反應(yīng)實(shí)例
Vinylcyclopentenes (3a) and (3b).To vinylcyclopropane 1 (150 mg, 0.68 mmol) and methyl butynoate 2 (1.26 g, 12.9 mmol) in PhH (6 mL) under Ar was added dropwise a deoxygenated solution of Ph2S2 (190 mg, 0.86 mmol) and AIBN (27 mg, 0,17 mmol) in PhH (40 mL) in ca 30 h under sunlamp irradiation. The mixture was kept at r.t. till 1 was consumed (TLC). Evaporation in vacuum
and flash chromatography (silica gel, 5% Et2O in hexane) afforded 96 mg of 3a and 3b in a 1.5:1 ratio (oil, 41%). Chromatography allows isolation of individual stereoisomers.
【Feldman KS, Tet Lett., 1989, 30, 5845】
相關(guān)文獻(xiàn)
1 Feldman KS J Am Chem Soc 1986 108 1328
2 Feldman KS J Am Chem Soc 1988 110 3300
3 Feldman KS J Am Chem Soc 1989 111 4878
4 Feldman KS Tet Lett 1989 30 5845
5 Feldman KS Tetrahedron 1989 45 2969
6 Feldman KS J Org Chem 1992 57 100
7 Singleton DA Synlett 1994 273
8 Byers JH Synth Comm 2007 37 1865
編譯自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 151.
